HCID 22675340, compound → HCID 22675302, compound

HRID 1006070Notes

Reaction equation

HRID 1006070 reaction equation
[Br:1][C:2]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][C:3]=1[CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][C:13]2[CH:14]=[C:15]([CH:35]=[CH:36][CH:37]=2)[C:16]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][O:27][Si](C(C)(C)C)(C)C)[CH:21]=2)=[O:17])[CH2:7][CH2:6]1>[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[Br:1][C:2]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][C:3]=1[CH2:4][CH:5]1[CH2:6][CH2:7][N:8]([CH2:11][CH2:12][C:13]2[CH:14]=[C:15]([CH:35]=[CH:36][CH:37]=2)[C:16]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][OH:27])[CH:21]=2)=[O:17])[CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 22675340HCID 22675340, compound

Product 1

HCID 22675302HCID 22675302, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

In tetra-n-butylammonium fluoride (a 1.0M THF solution, 5 mL, 5.0 mmol) was dissolved 3-{2-[4-(2-bromo-5-methoxybenzyl)-1-piperidinyl]ethyl}-N-[3-(tert-butyldimethylsiloxymethyl)benzyl]benzamide (389 mg, 0.584 mmol), and the resulting solution was stirred at room temperature for 2 hours. The reaction mixture was purified by the use of a silica gel column (silica gel 30 mL; ethyl acetate˜ethyl acetate/triethylamine=10/1) to obtain the desired compound (235 mg, 73%) as a yellow oil.

Workup

  1. customThe reaction mixture was purified by the use of a silica gel column (silica gel 30 mL; ethyl acetate˜ethyl acetate/triethylamine=10/1)

Sources & evidence

ORD record
ord-8951569b968a47a6b788dc0004cab6f5
Source dataset
uspto-grants-2004_09
Patent number
US06787560B2

Reaction notes

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